Antiproliferative Constituents in the Plant 8. Seeds of Rhynchosia volubilis.

Kinjo, Junei; Nagao, Tsuneatsu; Tanaka, Takashi; Nonaka, Gen‐ichiro; Okabe, Hikaru

doi:10.1248/bpb.24.1443

Cited by 24 publications

(29 citation statements)

References 13 publications

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“…As noted previously, compound 8 was reported to moderately inhibit the proliferation of B16F10 [8], HeLa [8], and MK-1 [8] cells and to be a moderately cytotoxic compound to HepG2 [9] and MRC-5 cells [11]. Compounds 6−10 exhibited significantly lower activity compared to 3,5-digalloyl-(-)-epicatechin (4 (-)-epigallocatechin (10), in which the number of hydroxyl groups on the B-ring was greater than that in 4, did not efficiently inhibit cell proliferation.…”

Section: Inhibitory Activity Against Cervical Epithelioid Carcinoma Csupporting

confidence: 63%

“…Since its first isolation from Sanguisorba officinals [4], there have been several reports regarding the isolation and biological activities of compound 8 as a minor constituent of Paeoniae obovate [7]; a moderate antiproliferation constituent against B16F10 [8], HeLa [8], and MK-1 [8]; a cytotoxic constituent against HepG2 [9] isolated from the seeds of Rhynchosia volubilis; and an antioxidant isolated from Acacia nilotica [10]. In addition, synthesis of 8 from a catechol-protected-(+)-catechin derivative, moderate antiplasmodial activity against FcB1, and cytotoxicity against MRC-5 cells were reported [11].…”

Section: Synthesismentioning

confidence: 99%

“…TBS-protected-7-hydroxyl-(+)-catechin derivative 14 was also condensed using 3,4,5-tribenzyloxybenzoic acid to give compound 18 with a 54% yield. Deprotection of the TBS ether of 18 using triethylamine trihydrofluoride gave compound 20 with an 88% yield, then hydrogenolysis of benzyl ether gave 7-galloyl-(+)-catechin (8) with an 83% yield (Scheme 1).…”

Section: Synthesismentioning

confidence: 99%

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Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Hojima¹,

Komeda²,

Higashino³

et al. 2017

Nat Prod Chem Res

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Flavan-3-ol derivatives are common plant-derived bioactive compounds with strong various biological activities. In particular, (-)-epigallocatechin-3-O-gallate exhibits a variety of moderate biological activities without severe toxicity. Its health-promoting effects have been widely studied because it is a main ingredient in green tea and is commercially available at low cost. In general, the galloyl moieties of flavan-3-ol derivatives are thought to be essential to their strong biological activities. However, it is not clear which position is most effective for modification with the galloyl moiety to strengthen the biological activities because various galloylated analogs are difficult to obtain in pure form in a quantity large enough for assays. Therefore, we synthesized various galloylated flavan-3-ol derivatives in a stereoselective and regioselective manner. We reported in a previous paper that 3,5-digalloyl-(-)-epicatechin displayed much stronger inhibitory activity than 3,5-digalloyl-(+)-catechin did against HeLa S3 cell proliferation. In this study, we describe synthetic studies of 7-galloyl-and 3,7-digalloyl-modified (-)-epicatechin and (+)-catechin and compared their biological activities, HeLa S3 cell proliferation inhibitory activity and DPPH radical scavenging activity with those of 3,5-digalloyl-(-)-epicatechin. The results indicated that 3,7-digalloyl derivative did not inhibit HeLa S3 cell proliferation. Furthermore, 3,5-digalloyl-(-)-epigallocatechin was synthesized to evaluate the importance of the number of phenolic hydroxyl groups on the B-ring. Contrary to our expectations, 3,5-digalloyl-(-)-epigallocatechin exhibited a weaker inhibition of HeLa S3 cell proliferation than 3,5-digalloyl-(-)-epicatechin did. The DPPH radical scavenging activity of the synthesized compounds suggested that the galloyl-modified position and the number of phenolic hydroxyl groups on B-ring affected to the radical scavenging ability. In conclusion, we found that 3,5-digalloyl-(-)-epicatechin exhibited a superlative HeLa S3 cell proliferation inhibitory effect among the galloylated flavan-3-ol derivatives we synthesized and DPPH radical scavenging activity was affected by the galloyl-moiety-introduced position and the number of phenolic hydroxyl groups on the B-ring.

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Section: Inhibitory Activity Against Cervical Epithelioid Carcinoma Csupporting

confidence: 63%

Section: Synthesismentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

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Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Hojima¹,

Komeda²,

Higashino³

et al. 2017

Nat Prod Chem Res

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“…For example, gallic acid and its analogs were reported from species such as R. volubilis and R. minima, isovitexin (flavonoid), and 8-C-prenylquercetin 7,4′-dimethyl ether (flavanol) were reported from the leaves of R. cyanosperma along with gallic acid derivatives. [15][16][17] These compounds are biologically important and proven to be active in a considerable number of pharmacological studies. [16][17][18][19] For example, antibacterial biphenyl constituents 4-(3-methyl-but-2-enyl)-5-methoxy-[1,1′ -biphenyl]-3-ol and 2-carboxy-4-(3-methyl-but-2-enyl)-5-methoxy-[1,1′-biphenyl]-3-ol were reported from R. suaveolens.…”

Section: Resultsmentioning

confidence: 99%

“…[15][16][17] These compounds are biologically important and proven to be active in a considerable number of pharmacological studies. [16][17][18][19] For example, antibacterial biphenyl constituents 4-(3-methyl-but-2-enyl)-5-methoxy-[1,1′ -biphenyl]-3-ol and 2-carboxy-4-(3-methyl-but-2-enyl)-5-methoxy-[1,1′-biphenyl]-3-ol were reported from R. suaveolens. 11 Therefore, it would be worth while carrying out a phytochemical investigation of R. scarabaeoides in order to isolate the active constituents responsible for the antibacterial activity found in the present study.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial properties of an Indian traditional medicinal plant, Rhynchosia scarabaeoides (L.) DC. (Fabaceae)

et al. 2011

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Rhynchosia scarabaeoides (L.) DC plant parts are extensively used by traditional healers in India to treat a variety of bacterial diseases, such as dysentery, diarrohea and skin disorders. This article reports the antibacterial activities of n-hexane, ethyl acetate and ethanol extracts belonging to the leaf, stem and root parts of R. scarabaeoides against five bacterial strains, Bacillus subtilis, Escherichia coli, Klebseilla pneumonia, Proteus vulgaris and Staphylococcus aureus, using an agar gel diffusion method. The range of inhibition zone (IZ) was found to be 15-24 mm and the minimum inhibitory activity (MIC) was found to be 1 mL/well. The IZ was found to be higher in ethyl acetate extracts while this was moderate in ethanol extracts, and no activity was seen with n-hexane extracts or root extracts. The MIC value of leaf ethyl acetate extract was found to be 1 mg against bacterial strains P. vulgaris and S. aureus, whereas 2 mg was found against B. subtilis, K. pneumoniae and E. coli. These results support the traditional usage of R. scarabaeoides plant parts in the treatment of bacterial infections. Interestingly, this plant was screened for antibacterial activity for the first time and was found to be active. Detailed chemical investigations are, therefore, warranted.

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Phytochemistry and pharmacological activities of the genus Rhynchosia: a comprehensive review

Rammohan

Reddy

Bhaskar

et al. 2019

Planta

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Antiproliferative Constituents in the Plant 8. Seeds of Rhynchosia volubilis.

Cited by 24 publications

References 13 publications

Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Antibacterial properties of an Indian traditional medicinal plant, Rhynchosia scarabaeoides (L.) DC. (Fabaceae)

Phytochemistry and pharmacological activities of the genus Rhynchosia: a comprehensive review

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